Bioinspired Total Synthesis of Hyperireflexolides A and B

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dc.contributor.authorzur Bonsen, A.B.
dc.contributor.authorSumby, C.J.
dc.contributor.authorGeorge, J.H.
dc.date.issued2023
dc.descriptionPublished: August 22, 2023
dc.description.abstractHyperireflexolides A and B were synthesized in six steps via the dearomatization and fragmentation of a simple acylphloroglucinol starting material. The dearomatized acylphloroglucinol undergoes a sequence of oxidative radical cyclization, retro-Dieckmann fragmentation, stereodivergent intramolecular carbonyl-ene reactions, and final α-hydroxy-β-diketone rearrangements to give the target natural products. This sequence is based on a biosynthetic proposal that claims the hyperireflexolides as highly rearranged polycyclic polyprenylated acylphloroglucinols (PPAPs), which is supported by the structural revision of hyperireflexolide B.
dc.description.statementofresponsibilityAndreas B. zur Bonsen, Christopher J. Sumby, and Jonathan H. George
dc.identifier.citationOrganic Letters, 2023; 25(34):6317-6321
dc.identifier.doi10.1021/acs.orglett.3c02232
dc.identifier.issn1523-7060
dc.identifier.issn1523-7052
dc.identifier.orcidzur Bonsen, A.B. [0000-0001-9111-3876]
dc.identifier.orcidSumby, C.J. [0000-0002-9713-9599]
dc.identifier.orcidGeorge, J.H. [0000-0002-7330-2160]
dc.identifier.urihttps://hdl.handle.net/2440/139346
dc.language.isoen
dc.publisherAmerican Chemical Society (ACS)
dc.relation.granthttp://purl.org/au-research/grants/arc/DP200102964
dc.rights© 2023 American Chemical Society
dc.source.urihttps://doi.org/10.1021/acs.orglett.3c02232
dc.subjectChemical synthesis; Fragmentation; Organic synthesis; Pharmaceuticals; Rearrangement
dc.titleBioinspired Total Synthesis of Hyperireflexolides A and B
dc.typeJournal article
pubs.publication-statusPublished

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